Colgate Sailing Adventures™

Adventure Sailing and Learning Vacations

As Offshore Sailing School enjoys its long legacy of continued education and adventure sailing vacation trips and programs, a host of exciting tried and true, and new, opportunities are available for Offshore Sailing School alumni, friends and sailors who want to keep on sailing. Founded in 1964 by renowned sailor, Steve Colgate, Offshore Sailing School has sailboat vacations and programs designed to open new horizons and special adventures for sailors everywhere. View a video recap of our 2019 “Dutch’s Insider’s Guide to the BVI” flotilla vacation here.

Offshore Cruising Club Flotilla Sailing Vacations

We have expanded our group sailing vacation packages that give you opportunities to see the world under sail. Originally just for Offshore alumni, these adventure vacations are open to all sailors who enjoy group sailing adventure trips. Known in sailing circles as “flotilla cruises,” these one week or longer group cruises are organized through Offshore Sailing School on fleets of sailboats all over the world. Whether you are new to sailing as an Offshore Sailing School alumni, or a seasoned sailor who wants to experience more, flotilla sailing vacation packages allow you to sign up, show up and get underway without the responsibilities of cruise organization. Read more about flotilla cruises here . . .Upcoming Sailing Trips

Girlfriend Getaways — Women Only Learn and Cruise Adventures

Heeding the call of women who want to take the helm with confidence, and following Doris Colgate‘s mantra to make sailing the ultimate self-esteem building adventure vacations for women, these special sailboat vacations provide educational opportunities for women to learn from expert women instructors in a supportive environment. Doris, our president and CEO, started the National Women’s Sailing Association and Women’s Sailing Foundation in 1990, and continues to be the driving force in putting women in control of their sailing destinies. Find more information on our sailing lessons for women only. View “Girls Gone Sailing” video here.

Racing Clinics for the Competitive Sailor

In April, our annual Offshore Sailing School/North U. Performance Race Week (sold out each year in November) takes on more innovation in its 20th season of collaboration between these two great educational institutions. Join us in 2020 at the beautiful Pink Shell Beach Resort on Fort Myers Beach, Florida. Guests are invited to join you for fun social events too!

Continuing Sailing Education (CSE)™

Even though you may have taken several courses with Offshore Sailing School or some other sailing organization, you never stop learning. The best sailors in the world will tell you there’s always something new to learn. Explore our many advanced course opportunities and sailing vacations. Try a Racing Course. Learn more about Navigation and Passage Making. Join a women-only cruising course. Sign up for our e-newsletter and stay in touch with Offshore Sailing School for new alumni courses and programs.

Offshore Sailing School Graduate Benefits

Contests with enticing prizes are held annually – some just for Offshore Sailing School graduates. The latest contest provided a FREE weeklong bareboat charter in the British Virgin Islands on a Moorings yacht for the lucky winner. Discounts with our partners provide you with excellent value. Alumni Benefits are just one way we say “thank you” for choosing Offshore Sailing School, and referring Offshore Sailing School to friends and family.

Support the Cause to Cure Blood Diseases

Offshore Sailing School is a national sponsor of The Leukemia & Lymphoma Society Leukemia Cup Regatta program. We invite you to join us in special events to raise money for this organization and other important causes. These are fun sailing activities that add to your sailing knowledge, and bring camaraderie and a sense of pride to all who participate. Check our News and Philanthropy pages and learn how you too can make a difference. We are celebrating our 10th year as a national sponsor and look forward to hosting the annual Leukemia Cup Regatta “Fantasy Sail” weekend in December 2019, at the beautiful Pink Shell Beach Resort & Marina on Ft. Myers Beach, Florida. Hopefully we’ll see you there as a top fundraiser supporting the need to find the cures for blood cancers!

Colgate 26

The Colgate 26 is used in all Learn to Sail, Performance Sailing and Racing courses. Designed by Steve Colgate and naval architect Jim Taylor, the Colgate 26 is a popular high performance keelboat, used to train plebes and cadets at the U.S. Naval and Coast Guard Academies, great for club racing and daysailing. Read more...

Newsletter Signup

The Offshore Sailing School newsletter is emailed twice a month to anyone interested in learning more about sailing and boating. It is packed with sailing and boating news, how-to tips, upcoming programs, contests and special deals.